2,2-二甲基-4-苯氧基-丁腈 | 100389-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2,2-二甲基-4-苯氧基-丁腈
• 英文名称: 2,2-dimethyl-4-phenoxybutanenitrile
• 英文别名: 2,2-dimethyl-4-phenoxy-butyronitrile
• CAS: 100389-77-3
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: YSASHRYADQMURQ-UHFFFAOYSA-N

物化性质

• 熔点：
  37-39 °C
• 沸点：
  91-95 °C(Press: 1 Torr)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-二甲基-4-苯氧基-丁腈 在 lithium aluminium tetrahydride 、 乙醚 、 水 、 氢溴酸 作用下， 生成 4-bromo-2,2-dimethyl-butylamine
  参考文献：
  名称：

  The Preparation of Geminally Substituted 4-Bromobutylamines. II. 4-Bromo-2,2-dialkyl- and diarylbutylamines¹

  摘要：

  DOI：

  10.1021/ja01610a002
• 作为产物：
  描述：

  异丁腈 、 2-苯氧乙基溴 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以95.2%的产率得到2,2-二甲基-4-苯氧基-丁腈
  参考文献：
  名称：

  Discovery of highly potent renin inhibitors potentially interacting with the S3′ subsite of renin

  摘要：

  To exploit the S3' subsite of renin active site for renin inhibitor design, 42 aliskiren derivatives with modified P2' portion were designed, synthesized and biologically evaluated. Some highly potent renin inhibitors (IC50 < 3 nM) were identified, among which compounds 38 (IC50 = 0.9 nM) and 39 (IC50 = 0.7 nM) were over 2.5-fold more potent than aliskiren (IC50 = 2.3 nM). SAR analysis indicated that incorporation of polar hydrophilic moieties into the P2' portion of renin inhibitors generally enhanced the potency. Consistently with this, molecular modeling study revealed that the triazole part of 39 could provide additional interactions to the S3' subsite of renin active site. Moreover, in vivo evaluation in the double transgenic mouse hypertension model demonstrated that 39 produced greater reduction of the mean arterial blood pressure than ariskiren at the doses of 17.0 and 34.0 mu mol/kg, respectively. Taken together, the S3' subsite of renin active site merits further consideration for renin inhibitor design. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.060

文献信息

• Lukes; Dedek, Collection of Czechoslovak Chemical Communications, 1958, vol. 23, p. 1981,1983
  作者：Lukes、Dedek

  DOI：——

  日期：——
• Lukes; Dedek, Chemicke Listy, 1957, vol. 51, p. 2139,2141
  作者：Lukes、Dedek

  DOI：——

  日期：——
• The Preparation of Geminally Substituted 4-Bromobutylamines. II. 4-Bromo-2,2-dialkyl- and diarylbutylamines¹
  作者：Ronald F. Brown、Norman M. van Gulick

  DOI：10.1021/ja01610a002

  日期：1955.3
• Discovery of highly potent renin inhibitors potentially interacting with the S3′ subsite of renin
  作者：Xiaowei Sun、Xiaoan Wen、Yan-yan Chen、Chen Shi、Chengzhe Gao、Yong Wu、Li-jun Wang、Xiu-hong Yang、Hongbin Sun

  DOI：10.1016/j.ejmech.2015.08.060

  日期：2015.10

  To exploit the S3' subsite of renin active site for renin inhibitor design, 42 aliskiren derivatives with modified P2' portion were designed, synthesized and biologically evaluated. Some highly potent renin inhibitors (IC50 < 3 nM) were identified, among which compounds 38 (IC50 = 0.9 nM) and 39 (IC50 = 0.7 nM) were over 2.5-fold more potent than aliskiren (IC50 = 2.3 nM). SAR analysis indicated that incorporation of polar hydrophilic moieties into the P2' portion of renin inhibitors generally enhanced the potency. Consistently with this, molecular modeling study revealed that the triazole part of 39 could provide additional interactions to the S3' subsite of renin active site. Moreover, in vivo evaluation in the double transgenic mouse hypertension model demonstrated that 39 produced greater reduction of the mean arterial blood pressure than ariskiren at the doses of 17.0 and 34.0 mu mol/kg, respectively. Taken together, the S3' subsite of renin active site merits further consideration for renin inhibitor design. (C) 2015 Elsevier Masson SAS. All rights reserved.